Chicago: What to see and do in 48 hours

Chicago is a city that combines rich history with a modern flare, from iconic architecture to world-class cuisine and from rooftop patios to trendy blues bars – something for everyone. A quick flight from Toronto, either Billy Bishop to Chicago Midway Airport, or from Pearson Airport to Chicago O’hare Airport and just over an hour later you are there. I recently had that chance to explore Chicago on a  48 hour’s girl’s trip, here are some of the things we’d recommend on your next visit:


Hotel stays: Where to stay in the city


We were lucky enough to stay in the newly opened Voco™ Chicago Downtown hotel, part of the  IHG Hotels & Resorts properties. This stylish hotel is located in the prime Wolf Point area (between North River, Fulton Market and the Loop) of Chicago,  directly attached to Chicago’s famous Merchandise Mart. The property is centrally located to some of the city’s top attractions including Millennium Park, the Magnificent Mile, Fulton Market, Navy Pier and the West Loop. The hotel combines a sense of elegance mixed with a trendy boutique vibe feel;; large enough to have key amenities like a gym, pool and a mini mart for late night snacks, but feels like a boutique hotel with a cozy restaurant, and lobby bar.  The hotel, built in a converted office building, makes clever use of the old building retrofitted to create hotel space in a trendy part of the city.  The rooms are large, and have a modern feel, comfortable beds, and big bathrooms. A great spot to start the night was the hotel  lobby bar, which was bustling with people getting a cocktail. If you are unable to snatch a room at this hotel, other areas in the city that are great include The loop, Wicker Park or Lincoln Park.


Architectural Marvels: A Skyline to Remember


Chicago boasts the second tallest skyline in the US and is a city filled with architectural glory; take a boat tour along the Chicago River to marvel at the city’s iconic skyscrapers, including the Willis Tower and John Hancock Center.  Here are two fun ways to take a river cruise:  either grab a cruise with the  Chicago CityPass on the Shoreline Sightseeing Boat as part of their three or five activity passes (priced from $96-$136). These passes allow you to pick other Chicago tourist sights to see while in town.  Another fun option is the Chicago Electric Boat Company; they offer self-guided and captained cruises and recently introduced a handful of boating options including an expanded retro boat fleet, Lakefront Cycle Boat cruises and guided tour cruises on. You can rent one of their stylish retro boats that are adorably refurbished 1950s and 1960s classics, in stunning colors like magenta, pink, and baby blue, as well as Cycleboats, for those looking to get a little exercise while enjoying views.


Culinary Delights: A Feast for the Senses

If you are a foodie, Chicago is  renowned for its diverse culinary scene; indulge in high end dining to deep-dish pizza at iconic pizzerias.  For a taste of the city’s diverse neighborhoods, explore the food markets like Chicago French Market and Revival Food Hall, and dine in the Fulton Market area. Don’t miss the chance to savor Chicago-style hot dogs or venture into the West Loop, home to some of the city’s trendiest restaurants.  Some of the our the tasty restaurants we lucky to try include:


Adorn Bar & Restaurant: The Four Seasons (120 E Delaware Pl)
Located on the main floor of the Four Seasons Hotel the restaurant is open daily for  dinner, lunch and weekend brunch. We visited for Saturday brunch, and experienced an exquisitely lavish food dining experience that was delicious with a fair price tag.  Adorn’s chef, Richie Farina (former host of Carnival Kings) with more than two decades experience (formally at two-Michelin-starred Ever, and one-Michelin-starred Moto) shaped his career in Chicago’s most inventive and lauded kitchens.  The menu is filled with brunch favourites: Avocado Toast, Egg Benedict Three Egg Omelet and Blueberry pancakes, but also has unique menu items such as: Tuna Poke Nachos, Breakfast Bao and Chilaquiles. We loved the Tuna Poke Nachos.


The Evie (535 N. Michigan Avenue)
The Evie, located in the Mag Mile, is owned by prominent veterans of the Chicago restaurant scene: George Archos and Chef-Partner Nick Nitti. The restaurant is all about delicious comfort food paired with an elegant dining in-style vibe; focusing on fresh, locally-sourced ingredients and high grade meats.  The restaurant has a supper club exclusive feel with floor-to-celing windows overlooking Michigan Ave. The food, something for every taste palette, from American classics (American Wagyu Chicago Style Hot Dog and Shrimp cocktail) to sushi and salads. We were lucky enough to share a variety of plates and all were exceptional.


Gino’s East – Deep-Dish Pizza Heaven (162 E. Superior St)


While Giordano’s and Lou Malnati’s are iconic for deep-dish pizza, Gino’s East is another heavyweight in the Chicago pizza scene. Known for its buttery crust, generous toppings, and artsy graffiti-covered walls, Gino’s East is a must-visit for pizza enthusiasts.


RPM Seafood:  (317 N. Clark St)

Located on the North River, RPM Seafood focuses on simple fresh seafood from around the world.  The restaurant is located with a beautiful view of the river, so you will be able to watch the riverboats and tours go by as you enjoy your meal.  The menu features Clam Chowder, Red Curry Lobster, Ora King Salmon and Fish Tacos.If you visit we recommend the Fish Tacos and Hawaiian Ono Ceviche.


Wildberry Pancakes and Cafe (two locations: 130 E Randolph St, and 196 E Pearson St)

Wildberry is a popular local brunch spot. Be sure to get there early or try to reserve a table,  as you can expect a queue at the door. The menu has options for bruch cravings. Try their Oreo S’mores Pancakes or the Los Altos Benedict.

RoofTop patios and Blues Bars:

From bars alongside the river to trendy rooftops bars and blues bars to live shows, Chicago has something for everyone. Catch a Broadway-caliber show in the famed Theater District or enjoy live music at iconic venues like the Chicago Symphony Orchestra or the House of Blues. For an authentic Chicago experience, immerse yourself in the city’s legendary blues scene at clubs like Blue Chicago.  Here are some places we enjoyed on our trip:


Chateau Carbide – Pendry Hotel (230 N Michigan Ave)

Located in the Pendry Hotel, an art-deco Carbide & Carbon building (golden champagne top), this roof-top exudes elegance and luxury. The building first opened in 1929 in the height of the Prohibition period. Once inside, the design feels like you have taken a  step back to the roaring 20’s. The rooftop is beautifully designed with comfortable seating, fireplaces, heaters and blankets so you can be cozy as you enjoy the views. The menu features drinks and a light serving of a seasonal food menu. The drinks, botanical-driven, absinthe-inspired offerings include cocktails, table side absinthe service, a thoughtfully curated absinthe collection as well as wines, beers and other mixed cocktails.


Virgin Hotel: Cerise (203 N Wabash Ave, Chicago, 60601)


Located in the Old Dearborn Bank Building (built in 1928) Ceriise is located on top of the trendy Virgin Hotel.  With almost 100 years of history, Virgin Hotels carefully renovated the building from basement to 26th floor, maintaining much of its original charm, but adding in modern elements. The food menu offers light bites including: Fried Chicken Sandwich, Shrimp Ceviche and Jumbo Wings.  The drink list includes wine, local beers and mixed cocktails.  This is another amazing view point looking over Chicago’s historic architectural skyline, including the Jewelers’ Building.



Blue Chicago (536 N Clark St,)

This local intimate spot is great for catching local blues. Located in the heart of the North River District, a little bit off the beaten path, but if you are able to catch a show here, you won’t be disappointed.  It is open five nights a week from 8 p.m. Be prepared to pay a cash cover at the door.



London House: (85 E Wacker Dr)


If you are looking for a glamorous rooftop where you can see a trendy Chicago crowd, this is one of the places to go. It is a tri-level rooftop overlooking the Michigan Avenue Bridge and the Chicago River.  The atmosphere is usually vibrant and fun and you can go for an afternoon tea or lunch. At night, you can sip one of their cocktails as you look at the Chicago skyline.  Be aware that this is one of Chicago’s most visited rooftops, so reservations are encouraged.

*header photo by Bhargava Marripati

Jessica Glover

An avid traveller and foodie, Jessica Glover loves travelling and exploring new cities either with friends or solo adventures. Some places she has travelled solo include India, South America, Asia and Europe. Jessica is always looking into the next trip and next adventure!

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